Route, Connections, Price: How Far Will You Go for a Cheap Flight?

I despise booking airfare. It's a laborious, tedious process rife with loopholes and changing price points that I don't understand. And I know — I just know — that as soon as I click “buy”, I'll find another fare (probably on a better airline no less) for a fraction of what I paid.

How to Find the Best Route

If you're short on travel time, then you probably don't want to go too far out of your way for a cheap flight. But don't just do a point A-B search; if you're flying from Miami to London, consider other major ports of departure (or arrival). It might be best to hop on a cheap flight to New York or Atlanta and catch a seat sale from there to London instead.

Personally I find this to be the most tedious part of the process, but a necessary evil. How do you search for alternate destination/arrival points? A few ways:

Widen Your Search

Many flight search engines have the ability to “search nearby airports.” Make sure this box is checked.

Consider Different Arrival and Departure Points

Popular routes often have seat sales. Search different major departure and arrival points (and if you can, be flexible with your flight dates/times).

Book Directly With the Airline

Once you've found a few airlines that fly your route, ditch the search engines and see what the airline's website has to offer. You might discover a seat sale that fits your needs.

How to Find the Best Connections

This is the biggest variable; one that, in conjunction with finding the best route, can result in the trip being a soul-destroying ordeal or a walk in the park. Much of it depends on what you're willing to pay for.

I made a trip from Toronto to Melbourne a few years ago that lasted over 50 hours. This is because I already had a cheap flight from New York, but I waited too long to find a connecting flight from Toronto to New York. I ended up taking an overnight bus and waiting the better part of a day in the airport, thus extending an already long trip by about 18 (unenjoyable) hours.

A subsequent trip from Auckland to Madrid took over 45 hours. Granted it's a long journey no matter which way you slice it, but since I was on a mission to fly in business class using my frequent flier miles, I conceded to spending 12 hours overnight in the Bangkok airport en route. (After sleeping on the airport floor for six hours, the business class lounge opened and I enjoyed a contrasting six hours getting free massages, free food, WiFi, and comfy lounge chairs. It was a good trade-off!)

Here are some tips for working out your connections.

Leave Time Between Connecting Flights

I despise missing connections. So I generally refuse to book a flight with anything less than a two-hour connection time. Even with this buffer I've found myself on delayed flights, tearing through the airport to make the connecting flight in time — with varying degrees of success.

Consider Other Forms of Transportation

Instead of doing a short-haul flight to connect to a longer one, it might be easier — and/or cheaper — to take a bus or train to/from your major departure/arrival point.

How to Find the Best Price

Price is usually the bottom line for people, but the question remains — how far will you go to get that cheap flight?

Last year I had to travel from Toronto to Fort Lauderdale. Following the route and connection tips above, I had a few options:

Fly from Toronto to Miami for $50 less, and contend with my Floridian friend's overwhelming distaste for the Miami airport and extra time on her part spent picking me up and dropping me off.

Fly from Buffalo to Fort Lauderdale on a super-budget airline for $150.

Really, the competition was between options one and three, since the $50 savings wasn't worth the hassle on my friend's part.

And since Buffalo is a mere two-hour drive from Toronto, it appeared that option three would be the best balance of routes, connections, and price.

Sadly, though, the airline's departure from Buffalo was at 7 a.m. (awkward flight times are a budget-airline signature). And I just couldn't find any way to get to Buffalo in time for that flight, shy of taking a bus the night before and either paying for a hotel or sleeping in the airport. The cost of the bus plus paying for a hotel would have negated the flight savings, and sleeping in the airport would have left me wrecked for my first few days in Florida.

And as much as I specialize in cheap full-time travel, if the cheapest option isn't remotely reasonable or comfortable, I'm happy to pay a little more (especially if I can collect valuable frequent flier miles in the process.

Budget airlines are an obvious option when searching for the best price. Here are a couple of other variables to consider in finding the best price.

Ditch the Search Engines

Search engines can be effective to get a general sense of what major airlines fly which routes, but they don't include many budget airlines and don't leave you privy to seat sales. Here's a technique I've used in the past to save up to 80% on airfare.

How Far Will You Go?

You'll notice that price, connections, and route are interrelated, yet conflicting — and most often confusing.

What are your experiences? How far out of your way (or comfort zone) would you go for a cheap flight? Are budget airlines really all they're cracked up to be after everything is said and done? And where is the line between saving money and being comfortable?

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Great Article! I find that minimizing travel time, even if it is the most expensive option is best. Less time in the air, means more time to adjust, more time to be productive, and more time to conduct business.

@Adam - I agree, if the trip is limited in time and/or for business, then sometimes it's worth the extra money to reduce travel time. (Unless, that is, you're really good at getting work done on planes...which interestingly, I'm not).

The part of me that loves hunting for deals tends to go into overdrive when searching for airfare, especially now that I live on the opposite coast from my family. While I agree that it can be good to book directly through the airline, lately I've been loving searching through Kayak. Their "hacker" fares, which pair one-way flights on two different airlines for a round-trip, are some of the cheapest options I've found.

I've never flown on a flight with more than one connecting stop. It is nerve wracking to me to even fly a one-stop flight because of the risks and headaches that come with catching a connection. That being said, I always have the nearby cities box checked when booking flights, because a lot of times you can get ones that are at least $100 less from a close city than the city you're actually flying out of. I live in Tampa now, and I actually found a flight from Orlando to Boston that was $150 cheaper than flying Tampa to Boston, and Orlando is only about an hour drive from here. I do just wish there was an airline like RyanAir in Europe though, flights from country to country can be as cheap as 5 euro! Granted the pilots are a little shady and landing feels like you might crash, but hey, you always get there alive!

@Kelly - I agree that searching nearby cities and airports are a great way to find cheaper fares. The only consideration however, is the cost of getting to/from the different airport.

I've flown with super-budget airlines in Europe like Ryan Air (and Easy Jet, and Vueling, etc) before, and it's certainly an experience! I particularly enjoy the mad scramble for seats on the plane, since my experience with Ryan Air is that there's no assigned seating.
But the cost is rarely the cost....there's always taxes, and fees for every little incidental from checked bags to carry on bags etc etc etc. If you play your cards right the fare is still inexpensive, but not as slamming a deal as it may seem at the outset.

Nora, I love this article! Great advice about using multiple connections, alternate airports and making the trip a journey if you have the time.

Though I may have outdone you on this on a couple of occasions. I just came back from Uruguay, temporarily to Colorado in the States, where my last leg was on a free Amtrak Guest Rewards train ticket from San Francisco! And the intercontinental legs were Montevideo Uruguay to Lima Peru, Lima to San Salvador El Salvador, and then my third flight to SFO.

A couple of years ago I flew from Raleigh-Durham NC to Spokane Washington via JFK, then from NYC to Toronto on South America's LAN airlines, then on Air Canada to Vancouver, AC Jazz to Seattle, and Alaska Airlines to Spokane. And yes, economically and in frequent flyer terms it made perfect sense. The JFK-YYZ LAN leg renewed all my LAN kilometers that were in danger of expiration from 3 years inactivity, YYZ-YVR-SEA on AC got me one more year of United Premier status, and that Seattle-Spokane on Air Canada helped me keep Alaska Airlines MVP elite status one more year. Which is also good for extra miles and benefits when flying on American and Delta. Plus I made a nice day and a half layover in Toronto, one of my favorite cities.

@Mark - You touch on two interesting concepts:
1) Enduring lengthy flight routes to get frequent flyer miles or special status on airlines you use a lot from which you can benefit from their perks, and
2) The joys of overland travel. I normally would take days on end of overland travel (and in fact, on many occasions I have voluntarily - and unnecessarily, and joyfully! - done so), but when combined with an extensive air travel agenda as well, I find it tiring.

Thank you! Traveling for more than 2 weeks is new to me, and the part I resist the most is booking the flight from Denmark to the US (even if it should be simple). It's good to know that it's not just me (even if I'm a solo soul) - and thanks so much for your great tips!